Scarlett Johansson as Annie Braddock

Laura Linney as Mrs. X

Alicia Keys as Lynette

Chris Evans as Hayden “Harvard Hottie”

Donna Murphy as Judy Braddock

Nicholas Art as Grayer

Judith Roberts as Milicent

Julie White as Jane Gould

Paul Giamatti as Mr. X

John Henry Cox as Dean

Lewis Payton, Jr. as Bike Messenger

Sonnie Brown as Human Resources Director

Georgina Chapman as TriBeCa Fashionista

Jodi Michelle Pynn as Screeching Lady

Mike Rad as Dude

Joanna Heimbold as Glamour Mom

Marla Sucharetza as Charity Mom

Phoebe Jonas as Xanax Mom

Allison Sarofim as Eating Disorder Mom

Tina Benko as Shopaholic Mom

Cady Huffman as Divorcing Mom

Kaitlin Hopkins as Bitsy

Reathel Bean as Doorman

Rosa Nino as Maria

Matilda Szydagis as Polish Nanny

Elle de Amor as Loud Nanny

Sakina Jaffrey as Sima

Alison Wright as Bridget

Nate Corddry as Calvin

Pete Heitmann as Guitar Player

Heather Simms as Murnel

Nina Garbiras as Miss Chicago

Melisa McGregor as Waitress

Rose Gonzalez as South American Nanny

Shalonne Lee as Jamaican Nanny

Ilana Levine as Whiny Mom

Isabel Keating as Paranoid Mom

Patrick Heusinger as Carter

Brendan Griffin as Kenny

Aaron Staton as John

Stephen O'Reilly as Reggie

Charlie Hewson as JoJo

Brande Roderick as Tanya

Nicola Barber as Lizzie

Kevin Kraft as Pierrot #1

Nicholas Alexiy Moran as Pierrot #2

James Urbaniak as Educational Consultant

Victoria Boothby as Matriarch

James Balsamo as Graduating Student (uncredited)

Michael Boothroyd as Waiter (uncredited)

David Boston as Parent at College Graduation (uncredited)

Tom Coughlin as Graduation Crowd Member (uncredited)

Deena Eddy as Upper East Side Shopper (uncredited)

L.J. Foley as Kid (uncredited)

Roy William Gardner as Golfer (uncredited)

Eli Harris as Lewis (uncredited)

Bobby Lundon as Darwin (uncredited)

Stella Stark as Nanny (uncredited)

Kimmy Suzuki as Flying Nanny (uncredited)

Dany Wolf as Yoga Teacher (uncredited)

Dianne Zaremba as Barmaid (uncredited)